What Kind Of Lunatic Travels To The Same Destination 36 Times?

This is the definition of insanity. Thankfully, there's a solution to such insanity.

My mother never understood why I wasted so much of my life returning to the same destination over and over. Fifteen years to be exact.

She’s the one-and-done type of traveller. Visit once and move on to the next place. That’s how you fill a passport worthy of bragging rights, isn’t it?

But what if the first time you visit a new place you fall madly in love? Not with a 90-Day-Fiance but with the actual city, state, province, or country.

What if you realize your trip barely even scratched the surface?

If you never go back you’ll never come to learn that you got ripped off on your airport taxi ride. You’ll never learn that jerk seasoning is supposed to burn your lips off. That’s how you know it’s authentic and not the watered-down tourist recipe.

And you’ll NEVER experience the exhilarating rush of Nascar-driving your rental car down the wrong side of roads that are legit too narrow for even one car.

(Okay, so those were pretty specific)

What I’m saying is, who cares if your passport is filled with 36 stamps from the same destination? Because FYI: That’s the secret to skipping routine immigration questions. Instead, they look at your passport and say, “Welcome home!”

It’s also how your favorite waitress at the airport arrivals bar magically appears, presenting your rum and Coke on a silver platter without you having to order it.

Okay, so it was Pepsi that one time, but still…

And yes, you CAN order liquor by the flask and mix your own drinks at bars in Jamaica.

It’s difficult to say whether I was so infatuated with Jamaica because it’s Jamaica or if I would have loved any old destination in the same way.

Jamaica was my first introduction to international travel. Obviously, it captivated me…I’m Canadian. We don’t have palm trees, colorful houses, or a vibrant dialect that sounds pleasant even when you’re telling someone to go suck it.

I can’t speculate what my life would have turned into if my first international travel had been to Prague or Nunavut.

However, I can say that I had previously been to San Diego and my life didn’t change at all. Not one bit. I pet a few dolphins at SeaWorld and called it a day.

Here’s how it began.

In March of 2003, I won my first all-inclusive vacation to Jamaica through a local radio station here in Canada. 

That five-day jaunt ruined my life as I knew it. 

If I’d never won the vacation that ignited my addiction in 2003, I probably would have owned a house, had a loaded bank account and had a wardrobe suitable for living in a city with eight months of winter. 

Instead, I moved back in with my mother, drove a 2000 Chevy Cavalier into the ground, wore the same four outfits all winter in order to maintain my much larger tropical attire, and had more luggage than I knew what to do with.

The vacation prize was pretty spectacular though! 

I stayed at an all-inclusive resort and went on scheduled bus trips to a bunch of different events during those five days. I ate and drank for free at the hotel, went to nightclubs, and visited tourist attractions. 

Sounds pretty typical, right?

But some very key occurrences happened on that trip which made me realize I’d seen a grand sum of nothing yet. 

Some of those key things were gazing out the tour bus window watching lively locals on gritty street corners gathered around pushcarts peddling everything from peanuts to pillows. And sizing up tiny wooden shacks dotting lush, tropical hillsides in the distance, wondering who on earth could live in dwellings like those.

I immediately knew this island wasn’t AT ALL about the strip of hotels and resorts I was on. I desperately wanted to get off the damn bus and become an indiscriminate thread woven into the fabric of such a colorful country.

Another key occurrence was that I clicked incredibly easily with the locals I’d met throughout those five days. Do you believe in past lives? Because I was probably Jamaican in at least one life.

One of the locals I met was a young police officer who made me an offer I simply couldn’t refuse.  He told me that if I ever returned to the island I could stay in his community in the countryside and he would show me the real Jamaica. 

Well honestly, who could turn down an offer like that?

A mere three months later, I returned to the island to cash in on his offer…and from there, the fifteen-year saga commenced.

Spur Tree Hill, Manchester, Jamaica

As years went by and my trip count to Jamaica approached double digits, it became obvious that I wasn’t the only one with this type of destination addiction. How did I know? Over time, I met hundreds of people, either virtually or in person, who also visited Jamaica on repeat. It’s the only place they ever went.

The difference between me and those people was that I became disgruntled very quickly with spending all my money on such an expensive habit. Something had to give but I didn’t understand what “something” was for many years.

I spent six years draining my bank account for the love of my addiction to Jamaica, until one cold, Canadian, November day I took a risk and sent a short email to an all-inclusive resort that changed everything.

When the results of that inquiry came back positive it was clear that I’d probably never have to pay for another vacation…ever. I’ve covered more on that here:

I realized that if you have to keep opening your wallet in exchange for Appleton rum and island fun, you’re doing it wrong. Something is broken.

Now, almost two decades later, I’ve calmed down long enough to flip through my crate full of journals and see that all the connections and discoveries I made out of necessity are totally worth sharing. If for no other reason than to pass the baton to other lunatics who can’t stop travelling to the same place over and over.

Right now, let’s make this about YOU.

I’d like to engage in getting to know about your guilty travel pleasures.  What’s your favorite destination? How many times have you been? (Even once counts!) Have you ever wished you could drop everything and move but you don’t know how on earth you’d ever survive on coconuts and pineapples?

Everyone wants someone to validate their questionable life choices, right?

~Kristi~

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Just for fun, check out one of the coolest things that could ever happen to you as a destination specialist: